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Chapter 16: Q20P (page 823)

Borazole, ,is an unusually stable cyclic compound. Propose a structure for borazole, and explain why it is aromatic.

Short Answer

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Resonance structure of borazole

Step by step solution

01

Borazole

Borazole is a non-carbon equivalent of benzene. The boron and nitrogen present in borazole is sp2hybridized and nitrogen has its pair of electrons in the p-orbital. Borazole is isoelectronic with benzene

02

Resonance structure for borazole

The borazole is usually stable cyclic compound d because of the presence of alternate pi electrons. Hence delocalization of structure is possible. Thus, it is stable because it follows the Huckel rule of 4n+2 where n is 1.

Resonance structure of borazole

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Most popular questions from this chapter

Question: For each NMR spectrum, propose a structure consistent with the spectrum and the additional information provided.

a. Elemental analysis shows the molecular formula to be C8H7OCl . The IR spectrum shows a moderate absorption at 1602 cm-1 and a strong absorption at 1690 cm-1 .

b.The mass spectrum shows a double molecular ion of ratio 1:1 at m/z 184 and 186.

Make a model of cyclooctatetraene in the tub conformation. Draw this conformation, and estimate the angle between the p orbitals of adjacent pi bonds

The proton NMR spectrum of 2-pyridone gives the chemical shifts shown.

(a) Is 2-pyridone aromatic?

(b) Use resonance forms to explain your answer to (a). Also explain why the protons at d 7.31 and d 7.26 are more deshielded than the other two (d 6.15 and d 6.57).

(c) Thymine is one of the heterocyclic bases found in DNA. Do you expect thymine to be aromatic? Explain.

(d) The structure of 5-fluorouracil is shown in the box at the side of the page. Is 5-fluorouracil aromatic? Explain.

Ciprofloxacin is a member of the fluoroquinolone class of antibiotics.

(a) Which of its rings are aromatic?

(b) Which nitrogen atoms are basic?

(c) Which protons would you expect to appear between d 6 and d 8 in the proton NMR spectrum?

Question: The benzene ring alters the reactivity of a neighboring group in the benzylic position much as a double bond alters the reactivity of groups in the allylic position.

Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates.

  1. Use resonance forms to show the delocalization (over four carbon atoms) of the positive charge, unpaired electron, and negative charge of the benzyl cation, radical, and anion.
  2. Toulene reacts with bromine in the presence of light to give benzyl bromide. Propose a mechanism for this reaction.

    c. Which of the following reactions will have the faster rate and give the better yield? Use a drawing of the transition state to explain your answer.
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